Dimethylamine (Me.sub.2NH) is reacted with sulfuryl fluoride (SO.sub.2F.sub.2) to form at least a first phase comprising N-(fluorosulfonyl) dimethylamine (FSO.sub.2NMe.sub.2), tetramethylsulfamide (SO.sub.2(NMe.sub.2).sub.2), or a combination thereof. A second phase, which may include dimethylamine hydrofluoride (Me.sub.2NH.sub.2F), may be also formed and separated from the first phase. FSO.sub.2NMe.sub.2 or SO.sub.2(NMe.sub.2).sub.2 is then isolated from the first phase. For example, the first phase may be a liquid phase, and FSO.sub.2NMe.sub.2 and SO.sub.2(NMe.sub.2).sub.2 are separated by distillation, optionally under reduced pressure.

An ionic diol has formula wherein R.sup.1 represents an alkyl group having from 6 to 18 carbon atoms; R.sup.2 and R.sup.3 independently represent alkyl groups having from 1 to 4 carbon atoms; R.sup.4 represents an alkylene group having from 2 to 8 carbon atoms; and R.sup.5 represents an alkylene group having from 1 to 8 carbon atoms. Antistatic polymers are formed by copolymerization of monomers including a diisocyanate, an ionic diol, a polyether diol, and at least one non-ionic diols. Methods of making the antistatic polyurethanes are also disclosed. ##STR00001##

An ionic diol has formula wherein R.sup.1 represents an alkyl group having from 6 to 18 carbon atoms; R.sup.2 and R.sup.3 independently represent alkyl groups having from 1 to 4 carbon atoms; R.sup.4 represents an alkylene group having from 2 to 8 carbon atoms; and R.sup.5 represents an alkylene group having from 1 to 8 carbon atoms. Antistatic polymers are formed by copolymerization of monomers including a diisocyanate, an ionic diol, a polyether diol, and at least one non-ionic diols. Methods of making the antistatic polyurethanes are also disclosed. ##STR00001##

The present application is directed to processes and intermediates for making 4-({2-[(aminosulfonyl)amino]ethyl}amino)-N-(3-bromo-4-fluorophenyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide, which is an inhibitor of indoleamine 2,3-dioxygenase, useful in the treatment of cancer and other disorders.

The present application is directed to processes and intermediates for making 4-({2-[(aminosulfonyl)amino]ethyl}amino)-N-(3-bromo-4-fluorophenyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide, which is an inhibitor of indoleamine 2,3-dioxygenase, useful in the treatment of cancer and other disorders.

Compounds of Formula (I) and pharmaceutically acceptable salts thereof, wherein G.sup.1, G.sup.2, G.sup.3, L.sup.1, L.sup.2, and L.sup.3 are as defined in the specification, are useful in treating conditions or disorders prevented by or ameliorated by the modulation of lysophosphatidic acid receptor 1. Methods for making the compounds are described. Also described are pharmaceutical compositions of compounds of formula (I), and methods for using such compounds and compositions.

##STR00001##

Compounds of Formula I, including pharmaceutically acceptable salts thereof, and compositions and methods for treating human immunodeficiency virus (HIV) infection are set forth: ##STR00001##

Compounds of Formula I, including pharmaceutically acceptable salts thereof, and compositions and methods for treating human immunodeficiency virus (HIV) infection are set forth: ##STR00001##

Dimethylamine (Me.sub.2NH) is reacted with sulfuryl fluoride (SO.sub.2F.sub.2) to form at least a first phase comprising N-(fluorosulfonyl) dimethylamine (FSO.sub.2NMe.sub.2), tetramethylsulfamide (SO.sub.2(NMe.sub.2).sub.2), or a combination thereof. A second phase, which may include dimethylamine hydrofluoride (Me.sub.2NH.sub.2F), may be also formed and separated from the first phase. FSO.sub.2NMe.sub.2 or SO.sub.2(NMe.sub.2).sub.2 is then isolated from the first phase. For example, the first phase may be a liquid phase, and FSO.sub.2NMe.sub.2 and SO.sub.2(NMe.sub.2).sub.2 are separated by distillation, optionally under reduced pressure.

Dimethylamine (Me.sub.2NH) is reacted with sulfuryl fluoride (SO.sub.2F.sub.2) to form at least a first phase comprising N-(fluorosulfonyl) dimethylamine (FSO.sub.2NMe.sub.2), tetramethylsulfamide (SO.sub.2(NMe.sub.2).sub.2), or a combination thereof. A second phase, which may include dimethylamine hydrofluoride (Me.sub.2NH.sub.2F), may be also formed and separated from the first phase. FSO.sub.2NMe.sub.2 or SO.sub.2(NMe.sub.2).sub.2 is then isolated from the first phase. For example, the first phase may be a liquid phase, and FSO.sub.2NMe.sub.2 and SO.sub.2(NMe.sub.2).sub.2 are separated by distillation, optionally under reduced pressure.